Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do?
Dear SaaStr: A Co-Founder is Asking for More Equity Post Fundraising. What Should I Do? Listen. It usually means something is wrong. Or at least, off: If you got the equity splits right at first, usually, big issues don’t come up later. This may be a sign you need to...
Dear SaaStr: What’s Your Top Advice For All New B2B Founders?
Dear SaaStr: As a VC, if you could go back to your operational experience (as part of a hyper-growth startup), then what would you remind yourself to take note of? My top list: Slow down big decisions — when you aren’t sure. You have to move fast and break things, but...
Dear SaaStr: My Startup is Nearing The End of its Runway – and I Found Out My CEO Has Been Taking Money from the Company. What Should I Do?
Dear SaaStr: My startup is nearing the end of its runway – and I found out my CEO has been taking money from the company. What should I do? Unfortunately, this is a little more common than you think. Maybe even more common today than a few years back, as VC...
Dear SaaStr: My Co-Founder Takes All The Public Credit. Should I be OK With This?
Dear SaaStr: My Co-Founder Takes All The Public Credit. Should I be OK With This? No, you shouldn’t. Not because it matters. But because clearly it’s gotten under your skin, which is a sign there’s some trouble here in your relationship with your...
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee?
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee? I’d suggest if you’re not sure where to draw the line … maybe don’t. It should be obvious. Founders are “there” before there is anything. Before a name. Before a product idea, usually. Before a...
Dear SaaStr: What is Your Best Advice for Maintaining Healthy Co-founder Relationships?
Dear SaaStr: What is Your Best Advice for Maintaining Healthy Co-founder Relationships? Talk. Dysfunctional co-founders don’t talk. Not for real. They stew. They get passive-aggressive. They email. They Slack. But they don’t talk. I don’t mean talk in group settings,...
5 Things to Do … When You Don’t Know What to Do
Best things to do when .. you don't know what to do: 1/ More time w/existing customers. Zoom w/5 week, meet 5/mo IRL 2/ Hire 1 great VP 3/ Drive down churn. You grow faster even w/o more leads 4/ Join more sales calls. Everyone loves talk to CEO 5/ Focus leads on...
The Tough Question Every CEO Must Answer: Would You Hire Every VP on Your Team Again?
Would you hire every VP on your team if you had to do it over again? If not, you know what you have to do Be Kind But get going — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 28, 2025 The Hardest Question Every CEO Must Answer: Would You Hire Every VP on Your Team...
CEO Compensation Today: Is It Broken? A Deep Dive With Brian Halligan Chair of HubSpot on What’s Wrong and How to Fix It
The uncomfortable truth about how we’re paying CEOs at the best tech companies wrong— and why it’s creating the wrong incentives for growth. A Candid Conversation with Brian Halligan Chair and Co-Founder of HubSpot on CEO Comp Reality We sat down on 20VC +...
How to Handle, and Share, Bad News
Run toward bad news Sometimes you need a moment. That's OK. But after that, hiding makes it worse. Process it … Then: Address itShare itTalk about itMake a planAct on it Your team and investors will rally — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin...
VPs That Can’t Hire … They Aren’t Real VPs. At Least, Not Yet.
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale —...
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested?
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested? Yes, it’s true but … #1. VCs Are Less Rigid Here Than They Used To Be If a deal is hot and you have multiple offers, VCs won’t push as hard here as...
A Simple Commitment Test For You And Your Co-Founders (Updated)
As we’ve talked about before, the great thing about SaaS is it compounds. Once you have something, it builds on itself. But it takes time. It takes 7-10 years to build something real. And probably 20 years to build something for the ages in SaaS. If all...
Dear SaaStr: What Are The Unspoken Downsides of Being a VC or Angel Investor?
Dear SaaStr: What Are The Unspoken Downsides of Being a VC or Angel Investor? Look the downsides are small folks. As a founder, you are often days away from total failure. This basically never happens for VCs, and even when it does, it happens over a decade+ (life of...
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